Ethyl cyanoacetate → HCID 135596636, compound

HRID 1288287Notes

Reaction equation

HRID 1288287 reaction equation
[Na].[C:2]([CH2:4][C:5](OCC)=[O:6])#[N:3].FS(O)(=O)=O.[CH:15]1([C:21]([NH2:23])=[NH:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C(O)C>[NH2:3][C:2]1[N:22]=[C:21]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[NH:23][C:5](=[O:6])[CH:4]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 5360545SodiumHCID 86734094HCID 86734094, compound

Product 1

HCID 135596636HCID 135596636, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of sodium (8.0 g.) in dry ethanol (150 ml.) was added ethyl cyanoacetate (12 ml.) followed after 15 minutes by crude cyclohexanecarboxamidine fluorosulphonate (10 g.). The mixture was heated under reflux for 20 hours, evaporated to half volume, water (100 ml.) was added and the pH adjusted to 6 by the addition of glacial acetic acid. After cooling to 0° C, the solid was filtered off and washed with water and acetone to give 4-amino-2-cyclohexylpyrimid-6-one (18 g.), m.p. 274°-276° C. (with decomposition).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 hours
  3. customevaporated to half volume, water (100 ml.)
  4. additionwas added
  5. additionthe pH adjusted to 6 by the addition of glacial acetic acid
  6. filtrationthe solid was filtered off
  7. washwashed with water and acetone

Sources & evidence

ORD record
ord-2b7cc87bab01467fbb31874f41c8207e
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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